LBF20406LT02: Difference between revisions

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{{Lipid/Header}}
{{Hierarchy|{{PAGENAME}}}}
{{Hierarchy|{{PAGENAME}}}}
{{Lipid/Header}}


{{Metabolite
{{Metabolite
|LipidBank=XPR3101
|LipidBank=XPR3101
|LipidMaps=LMFA03020001
|LipidMaps=LMFA03020001
|SysName=5 (S) ,12 (R) -Dihydroxyeicosa-6 (Z) ,8 (E) ,10 (E) ,14 (Z) -tetraenoic acid
|SysName=(5S,12R) -Dihydroxy- (cis-6,trans-8,trans-10,cis-14) -eicosatetraenoic acid
|Common Name=&&LEUKOTRIENE B4&&5 (S) ,12 (R) -Dihydroxyeicosa-6 (Z) ,8 (E) ,10 (E) ,14 (Z) -tetraenoic acid&&
|Common Name=&&Leukotriene B_4&&(5S,12R) -Dihydroxy- (6Z,8E,10E,14Z) -eicosatraenoic acid&&5 (S) ,12 (R) -Dihydroxyeicosa-6 (Z) ,8 (E) ,10 (E) ,14 (Z) -tetraenoic acid&&
|Solubility=METHANOL [[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]]
|Solubility=METHANOL [[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]]
|Mass Spectra=m/e 336, 319, 301 [[Reference:Yergey_JA:Kim_HY:Salem_N_Jr:,Anal. Chem.,1986,58,1344|{{RelationTable/GetFirstAuthor|Reference:Yergey_JA:Kim_HY:Salem_N_Jr:,Anal. Chem.,1986,58,1344}}]]
|Mass Spectra=m/e 336, 319, 301 [[Reference:Yergey_JA:Kim_HY:Salem_N_Jr:,Anal. Chem.,1986,58,1344|{{RelationTable/GetFirstAuthor|Reference:Yergey_JA:Kim_HY:Salem_N_Jr:,Anal. Chem.,1986,58,1344}}]]
|UV Spectra=METHANOL : 260(<FONT FACE="Symbol">e</FONT> 38,000), 270.5(<FONT FACE="Symbol">e</FONT> 50,000), 281(<FONT FACE="Symbol">e</FONT> 39,000)nm [[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]]
|UV Spectra=METHANOL : 260( epsilon  38,000), 270.5( epsilon  50,000), 281( epsilon  39,000)nm [[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]]
|NMR Spectra=<SUP><FONT SIZE=-1>1</FONT></SUP>H-NMR(250MHz, D<SUB><FONT SIZE=-1>2</FONT></SUB>O) : <FONT FACE="Symbol">d</FONT> 6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) [[Reference:Merrer_YL:Gravier-Pelletier_C:Micas-Languin_D:Mestre_F:Durreault_A:Depezay_JC:,J. Org. Chem.,1989,54,2409|{{RelationTable/GetFirstAuthor|Reference:Merrer_YL:Gravier-Pelletier_C:Micas-Languin_D:Mestre_F:Durreault_A:Depezay_JC:,J. Org. Chem.,1989,54,2409}}]]
|NMR Spectra=^1 H-NMR(250MHz, D_2 O) : delta  6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) [[Reference:Merrer_YL:Gravier-Pelletier_C:Micas-Languin_D:Mestre_F:Durreault_A:Depezay_JC:,J. Org. Chem.,1989,54,2409|{{RelationTable/GetFirstAuthor|Reference:Merrer_YL:Gravier-Pelletier_C:Micas-Languin_D:Mestre_F:Durreault_A:Depezay_JC:,J. Org. Chem.,1989,54,2409}}]]
|Source=Leukotriene B4 is produced by polymorphonuclear leukocytes and macrophages of various animal species upon various stimulations on the cells [[Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1|{{RelationTable/GetFirstAuthor|Reference:Samuelsson_B:Hammarstrom_S:,Vitam. Horm.,1982,39,1}}]][[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]].
|Chemical Synthesis=[[Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984|{{RelationTable/GetFirstAuthor|Reference:Corey_EJ:Marfat_A:Goto_G:Brion_F:,J. Am. Chem. Soc.,1980,102,7984}}]] {{Image200|LBF20406LT02FT0001.gif}}
|Metabolism=Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee B4 by leukotriene A hydrolase [[Reference:Ford-Hutchinson_AW:Gresser_M:Young_RN:,Annu. Rev. Biochem.,1994,63,383|{{RelationTable/GetFirstAuthor|Reference:Ford-Hutchinson_AW:Gresser_M:Young_RN:,Annu. Rev. Biochem.,1994,63,383}}]]. Leukotriene B4 is metabolized to lose its bioactivities either by  omega -oxidation [[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]] or by leukotriene B4 12-hydroxydehydrogenase [[Reference:Yokomizo_T:Izumi_T:Takahashi_T:Kasama_T:Kobayashi_Y:Sato_F:Taketani_Y:Shimizu_T:,J. Biol. Chem.,1993,268,18128|{{RelationTable/GetFirstAuthor|Reference:Yokomizo_T:Izumi_T:Takahashi_T:Kasama_T:Kobayashi_Y:Sato_F:Taketani_Y:Shimizu_T:,J. Biol. Chem.,1993,268,18128}}]].
|Symbol=LTB4
|Biological Activity=Leukotriene B4 causes adhesion of leukocytes to endothelial cells, stimulates chemotaxis and chemokinesis of leukocytes[[Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355|{{RelationTable/GetFirstAuthor|Reference:Hammarstrom_S:,Annu. Rev. Biochem.,1983,52,355}}]], and enhances superoxide anion production by human polymorphonuclear leukocytes [[Reference:Sumimoto_H:Takeshige_K:Minakami_S:,Biochim. Biophys. Acta,1984,803,271|{{RelationTable/GetFirstAuthor|Reference:Sumimoto_H:Takeshige_K:Minakami_S:,Biochim. Biophys. Acta,1984,803,271}}]]. Leukotriene B4 binds to a specific receptor with 7 transmembrane domains coupled to Gi/Go or Gq protein [[Reference:Yokomizo_T:Izumi_T:Chang_K:Takuwa_Y:Shimizu_T:,Nature,1997,387,620|{{RelationTable/GetFirstAuthor|Reference:Yokomizo_T:Izumi_T:Chang_K:Takuwa_Y:Shimizu_T:,Nature,1997,387,620}}]].
|Genetic Information=cDNA and genomic DNA of 5-lipoxygenase [[Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67|{{RelationTable/GetFirstAuthor|Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67}}]] and cDNA for Leukotriene A hydrolase [[Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67|{{RelationTable/GetFirstAuthor|Reference:Funk_CD:,Prog Nucleic Acid Res Mol Biol.,1993,45,67}}]] were cloned. cDNA for leukotriene B 12-hydroxydehydrogenase was cloned [[Reference:Yokomizo_T:Ogawa_Y:Uozumi_N:Kume_K:Izumi_T:Shimizu_T:,J. Biol. Chem.,1996,271,2844|{{RelationTable/GetFirstAuthor|Reference:Yokomizo_T:Ogawa_Y:Uozumi_N:Kume_K:Izumi_T:Shimizu_T:,J. Biol. Chem.,1996,271,2844}}]].
}}
 
{{MassbankSpectra|
UT000280
UT000281
UT000282
UT000283
UT000284
UT000285
UT000286
UT000287
UT000288
}}
}}


{{Lipid/Footer}}
{{Lipid/Footer}}

Latest revision as of 00:00, 17 January 2014

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Upper classes: LB LBF



Leukotriene B4
LBF20406LT02.png
Structural Information
(5S,12R) -Dihydroxy- (cis-6,trans-8,trans-10,cis-14) -eicosatetraenoic acid
  • Leukotriene B4
  • (5S,12R) -Dihydroxy- (6Z,8E,10E,14Z) -eicosatraenoic acid
  • 5 (S) ,12 (R) -Dihydroxyeicosa-6 (Z) ,8 (E) ,10 (E) ,14 (Z) -tetraenoic acid
LTB4
Formula C20H32O4
Exact Mass 336.23005951199997
Average Mass 336.46567999999996
SMILES C(CC=CC[C@H](C=CC=CC=C[C@H](CCCC(O)=O)O)O)CCC
Physicochemical Information
METHANOL Corey_EJ et al.
Leukotriene B4 is produced by polymorphonuclear leukocytes and macrophages of various animal species upon various stimulations on the cells Samuelsson_B et al. Hammarstrom_S .
Corey_EJ et al.
LBF20406LT02FT0001.gif
Arachidonic acid is metabolized to leukotrienen A4 with 5,6-epoxide by 5-lipoxygenases, and the product is further transformed to leukotrienee B4 by leukotriene A hydrolase Ford-Hutchinson_AW et al.. Leukotriene B4 is metabolized to lose its bioactivities either by omega -oxidation Hammarstrom_S or by leukotriene B4 12-hydroxydehydrogenase Yokomizo_T et al..
Leukotriene B4 causes adhesion of leukocytes to endothelial cells, stimulates chemotaxis and chemokinesis of leukocytes Hammarstrom_S , and enhances superoxide anion production by human polymorphonuclear leukocytes Sumimoto_H et al.. Leukotriene B4 binds to a specific receptor with 7 transmembrane domains coupled to Gi/Go or Gq protein Yokomizo_T et al..
cDNA and genomic DNA of 5-lipoxygenase Funk_CD and cDNA for Leukotriene A hydrolase Funk_CD were cloned. cDNA for leukotriene B 12-hydroxydehydrogenase was cloned Yokomizo_T et al..
Spectral Information
Mass Spectra m/e 336, 319, 301 Yergey_JA et al.
UV Spectra METHANOL : 260( ε 38,000), 270.5( ε 50,000), 281( ε 39,000)nm Corey_EJ et al.
IR Spectra
NMR Spectra 1H-NMR(250MHz, D2O) : δ 6.45(m, 1H, 8-CH), 6.15(m, 2H, 9,10-CH), 6.0(m, 1H, 7-CH), 5.65(m, 1H, 11-CH), 5.40(m, 1H, 15-CH), 5.25(m, 2H, 6,14-CH), 4.60(5-CH), 4.05(m, 1H, 12-CH), 2.15(m, 2H, 13-CH), 2.00(m, 1H, 2-CH), 1.85(m, 2H, 16-CH), 1.35-1.60(m, 4H, 3,4-CH), 1.00-1.25(m, 6H, 17,18,19-CH), 0.70(m, 3H, 20-CH) Merrer_YL et al.
Other Spectra
Chromatograms
Reported Metabolites, References
Biospecies ID Compound Name Reference Comment
n.a. LBF20406LT02 See above. Corey_EJ et al. 1980
n.a. LBF20406LT02 See above. Ford-Hutchinson_AW et al. 1994
n.a. LBF20406LT02 See above. Funk_CD 1993
n.a. LBF20406LT02 See above. Hammarstrom_S 1983
n.a. LBF20406LT02 See above. Merrer_YL et al. 1989
n.a. LBF20406LT02 See above. Samuelsson_B et al. 1982
n.a. LBF20406LT02 See above. Sumimoto_H et al. 1984
n.a. LBF20406LT02 See above. Yergey_JA et al. 1986
n.a. LBF20406LT02 See above. Yokomizo_T et al. 1997
n.a. LBF20406LT02 See above. Yokomizo_T et al. 1993
n.a. LBF20406LT02 See above. Yokomizo_T et al. 1996